45th Austrian Chemistry Olympiad

National Competition

Practical Tasks
May 31st, 2019

Solutions
45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions
Problem 8 83 bp ≜ 21 rp

Analysis of Wine

Analysis of red wine 1 (RW1): Determining the color of red wine

8.1 Specify your results

A420 = 1.866 1.5bp* A520 =2.165 1.5bp* A620 = 0.506 1.5bp*

FI = 4.536 0.5 bp FT = 0.8640 0.5 bp

8.2 Tick the boxes to give your assessment of the wine.

Wine color is X weak  good  very good

0.5bp

The wine seems to be  young X matured  strongly matured

0.5bp

* ΔA = |AStudent-AMasterValue|

∆ A−0.005
if ΔA < 0.005 → 1.5bp; if ΔA > 0.06 → 0bp; otherwise bp=1.5∗ 1− ( 0.055 )
Analysis of red wine 2 (RW2): Determining reducing sugars
8.3 Specify your results.

Vbl = 15.2mL 15bp* VZ = 12.7mL 15bp** Sugar content 4.50 g /L

0.5bp

For this experiment, thiosulfate concentration was c(Na 2S2O3) = 0.100mol/L

ΔV = |VStudent-VMasterValue|

∆V −0.20
* ΔV < 0.20mL → 15bp; if ΔV > 0.75mL → 0bp; otherwise bp=15∗ 1− ( 0.55 )
∆V −0.25
** ΔV < 0.25mL → 15bp; if ΔV > 0.80mL → 0bp; otherwise bp=15∗ 1− ( 0.55 )

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions

Analysis of white wine 1 (WW1): Determining the content of free sulfurous acid
8.4 State your titration volumes und give the SO2 content of the wine in mg/L.

V1 = 3.91mL 10bp* V2 = 0.62mL 12bp* free SO2: 26.37 mg/L 2bp

For this experiment, iodate concentration was c(KIO3) = 0.417mmol/L

ΔV = |VStudent-VMasterValue|
∆V −0.05
* ΔV < 0.05mL → 10bp; if ΔV > 0.80mL → 0bp; otherwise bp=10∗ 1− ( 0.75 )
∆ V −0.02
** ΔV < 0.02mL → 12bp; if ΔV > 0.25mL → 0bp; otherwise bp=12∗ 1− ( 0.23 )
Analysis of white wine 2 (WW2): Determining the extract content
8.5 Specify your results.

Ρwater = 0.99492 g/mL ρ sample = 1.00159 g/mL 10bp*

ρrel = 1.0067 0.5bp Extract = 17.22 g/L 2.5bp

Δρrel = |ρStudent-ρ MasterValue|(the Jury calculates ρrel from ρwater and ρwine. If the student calculates
correctly themselves, they receive 0.5 bp)

∆¿ rel−0.0015
* Δρrel < 0.0015 → 10bp; if Δρrel > 0.0070mL → 0bp; otherwise bp=10∗ 1− ( 0.00550 )
Analysis of white wine 3 (WW3): Determining titratable acid
8.6 Specify your titration volume and the content of tartaric acid in the wine in g/L.

V = 0.7mL 7bp* Content tartaric acid: 5.18 g/L 1.5bp

ΔV = |VStudent-VMasterValue|

∆ V −0.01
* ΔV < 0.01mL → 7bp; if ΔV > 0.10mL → 0bp; otherwise bp=7∗ 1− ( 0.09 )
8.7 Bromothymol blue is a useful indicator, because …. (tick correct answers).

□ the color change is well visible (yellow – green - blue).

□ it is non-toxic and hence does not spoil the wine sample.
X its pKa is 7.1. 0.5bp

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions

□ its pKa is 9.3.

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions
Problem 9 15 bp ≜ 4 rp

A little Photometry

9.1 Specify the absorbtion maximum λmax and the corresponding absorbance of your
hydrazone. Write at least 10 pairs of values into the table.

Photometer A: λmax: 377.5 nm (respective absorbance: 1.52)

Photometer B: λmax: 384 nm (respective absorbance: 1.25)

Photometer C: λmax: 377 nm (respective absorbance: 1.57) (3.5 + 1.5 bp)

Measure
ment Lambda A

1. 350 1

2. 400 1.25

3. 450 0.4

4. 500 0.06

5. 360 1.28

6. 370 1.46

7. 380 1.5

8. 390 1.44

9. 375 1.51

10. 385 1.45

11. 377 1.52

12. 378 1.52

13. 376 1.52

14. 379 1.52

5 bp for 10 measured values 10 bp

9.2 Draw the absorption spectrum and label abscissa and ordinate.

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions

Photometer A
1.6

1.4

1.2

0.8

0.6

0.4

0.2

0
300 320 340 360 380 400 420 440 460 480 500

Abszissa: wavelength [nm] Ordinate: Absorbance 2+3bp

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions
Problem 10 56.5 bp ≜ 15 rp

Synthesis: Derivatization of carbonyl compounds to achieve semicarbazones

Synthesis of the raw product:

10.1 Show your raw product as well as the mass you measured in the weighing room to a lab
supervisor for affirmation..

Assessment of yield 0-10 bp*

*If 0.2665 g ≤m RP ≤ 0.295 g → 10 bp; if m RP > 0.295 g → 0 bp

mRP
otherwise: bp=10 ⋅ ( 0.2665);

Reprocessing and purification:

10.2 Show product as well as the mass you measured in the weighing room to a lab supervisor for
affirmation.

Assessment of yield 25 bp*

*If 0.222 ≤ m P ≤ 0.295 → 25 bp; if m P > 1→ 0 bp

m
otherwise: bp=25 ⋅ ( 0.222 );
P

Apperance of the product: 0-3 bp

Evaluation and control of purity:

10.3 Determine yield in g and % of theory.

177.20
theor. yield.: m = 0.2 ∙ =0.295 g
120.15
mp
own yield in %= ∙ 100=… % 2 bp
0.295
10.4 Determine the melting point and choose your unknown carbonyl compound from the list.
Show your experiment for determining the melting point to a laboratory supervisor directly
on the Kofler bench.

Melting point: ___________ (208-210) 0-3 bp

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45th Austrian Chemistry Olympiad – National Competition Practical Tasks - Solutions
Correct assignment of carbonyl compound 1 bp

Analysis

10.5 Specify the following Rf values:

Rf-value of educt: 0.84 Rf-value of raw product: 0.35 Rf-value product: 0.35 3 bp
Assessment of TLC:
Two lines, labelling 2 bp
Size of spots, marking the spots on the plate 5 bp

10.6 Tick the correct statement(s)

The Educt E has □ lower □ higher Rf value, than the Product P , because …
□ E forms stronger H-bonds with silica gel.
□ E forms intramolecular H-bonds.
X P forms stronger H-bonds with silica gel.
□ P has higher molar mass.
□ P is less polar.
X E is less polar.
X Silica gel is also polar.
X Silica gel forms stronger interactions with P.
0.5 bp per correctly ticked box,– 0.5bp per incorrectly ticked box. min 0 bp max. 2.5 bp